Abstract
Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1138-1147 |
| Number of pages | 10 |
| Journal | Chemistry of Heterocyclic Compounds |
| Volume | 43 |
| Issue number | 9 |
| DOIs | |
| State | Published - Sep 2007 |
| Externally published | Yes |
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Keywords
- 1,1-dihydropolyfluoroalkyl sulfone
- N-chlorotriazole
- V-triazole
- X-ay structural analysis
ASJC Scopus subject areas
- Organic Chemistry
Cite this
4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. / Bandera, Yu P.; Kanishchev, O. S.; Timoshenko, V. M.; Buth, Sergii; Nesterenko, A. M.; Shermolovich, Yu G.
In: Chemistry of Heterocyclic Compounds, Vol. 43, No. 9, 09.2007, p. 1138-1147.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - 4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles
AU - Bandera, Yu P.
AU - Kanishchev, O. S.
AU - Timoshenko, V. M.
AU - Buth, Sergii
AU - Nesterenko, A. M.
AU - Shermolovich, Yu G.
PY - 2007/9
Y1 - 2007/9
N2 - Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.
AB - Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4- (p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N-Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5- polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5- polyfluoroalkyl-2H-[1,2,3]triazoles.
KW - 1,1-dihydropolyfluoroalkyl sulfone
KW - N-chlorotriazole
KW - V-triazole
KW - X-ay structural analysis
UR - http://www.scopus.com/inward/record.url?scp=36949021324&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=36949021324&partnerID=8YFLogxK
U2 - 10.1007/s10593-007-0175-x
DO - 10.1007/s10593-007-0175-x
M3 - Article
VL - 43
SP - 1138
EP - 1147
JO - Chemistry of Heterocyclic Compounds
JF - Chemistry of Heterocyclic Compounds
SN - 0009-3122
IS - 9
ER -